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dc.contributor.authorWalton, John Christopher
dc.contributor.authorManley, David W.
dc.contributor.authorMills, Andrew
dc.contributor.authorO'Rourke, Christopher
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.date.accessioned2014-03-27T10:01:02Z
dc.date.available2014-03-27T10:01:02Z
dc.date.issued2014-03-20
dc.identifier.citationWalton , J C , Manley , D W , Mills , A , O'Rourke , C & Slawin , A M Z 2014 , ' Catalyst-free photoredox addition–cyclisations : exploitation of natural synergy between aryl acetic acids and maleimide ' Chemistry - A European Journal , vol. 20 . https://doi.org/10.1002/chem.201304929en
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 106066694
dc.identifier.otherPURE UUID: a429bde9-e114-4007-9f3e-ed2582fd1826
dc.identifier.otherScopus: 84899644662
dc.identifier.otherORCID: /0000-0003-2746-6276/work/56638696
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861516
dc.identifier.urihttp://hdl.handle.net/10023/4543
dc.descriptionThis work was funded by EPSRC Grant Numbers: EP/I003479/1, EP/I003800/2. The paper was made open accees through RCUK block grant funds.en
dc.description.abstractSuitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy.
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rights© 2014 The Authors. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectEPR spectroscopyen
dc.subjectHeterocyclic compounden
dc.subjectNMR spectroscopyen
dc.subjectPhotochemistryen
dc.subjectRadicalsen
dc.titleCatalyst-free photoredox addition–cyclisations : exploitation of natural synergy between aryl acetic acids and maleimideen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/chem.201304929
dc.description.statusPeer revieweden


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